Cascade reactions of substituted 1,2,4-triazines: Rapid access to nitrogen-containing polycycles

Journal of the American Chemical Society

Volumn 126, Issue 39, 2004, Pages 12260-12261

  Raw, Steven A ^a   Taylor, Richard J K ^a  

^a UNIVERSITY OF YORK   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

1,2,4 TRIAZINE DERIVATIVE; ALLYLAMINE; CYCLOBUTANONE DERIVATIVE; CYCLOPENTANONE DERIVATIVE; DIHYDROPYRIDINE DERIVATIVE; ENAMINE; IMINE; NITROGEN DERIVATIVE; POLYCYCLIC HYDROCARBON;

ARTICLE; DIASTEREOISOMER; DIELS ALDER REACTION; ELECTRON; STEREOCHEMISTRY; SUBSTITUTION REACTION; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

EID: 4644332694     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja045780g     Document Type: Article

References (23)

1. (a) Raw, S. A.; Wilfred, C. D.; Taylor, R. J. K. Org. Biomol. Chem. 2004, 2, 788-796.
2. (b) Raw, S. A.; Wilfred, C. D.; Taylor, R. J. K. Chem. Commun. 2003, 2286-2287.
3. (c) McManus, J. C.; Carey, J. S.; Taylor, R. J. K. Synlett 2003, 365-368.
4. (d) McManus, J. C.; Genski, T.; Carey, J. S.; Taylor, R. J. K. Synlett 2003, 369-371.
5. For example, see: (a) Neunhoffer, H. In Comprehensive Heterocyclic Chemistry II; Katritzky, A. R., Rees, C. W., Scriven, E. F. V., Eds.; Pergamon: Oxford, 1996; Vol. 6, Chapter 6.11, pp 507-573.
6. (b) Neunhoffer, H In Comprehensive Heterocyclic Chemistry; Katritzky, A. R., Rees, C. W., Eds.; Pergamon: Oxford, 1984; Vol. 3, Chapter 2.19, pp 385-456.
7. (c) Boger, D. L.; Weinreb, S. N. Hetero Diels-Alder Methodology in Organic Synthesis; Academic Press: London, 1987; Chapter 10, pp 300-358.
8. (d) Boger, D. L. Tetrahedron 1983, 39, 2869-2939.
9. (a) Chenard, B. L.; Ronau, R. T. J. Org. Chem. 1988, 53, 5175-5177.
10. (b) Boger, D. L.; Panek, J. S. J. Org. Chem. 1981, 46, 2179-2182.
11. (c) Boger, D. L.; Panek, J. S.; Meier, M. M. J. Org. Chem. 1982, 47, 895-897.
12. The unusual stability of some dihydropyridines 2 to aromatization has been reported.3
13. Raw, S. A.; Taylor, R. J. K. Chem. Commun. 2004, 508-509.
14. For examples, see: (a) Wei, X.; Taylor, R. J. K. J. Org. Chem. 2000, 65, 616-620.
15. (b) Raw, S. A.; Reid, M.; Roman, E.; Taylor, R. J. K. Synlett 2004, 819-822.
16. (c) Blackburn, L.; Kanno, H.; Taylor, R. J. K. Tetrahedron Lett. 2003, 44, 115-118.
17. (d) Runcie, K. A.; Taylor, R. J. K. Chem. Commun. 2002, 974-975.
18. (e) Outram, H. S.; Raw, S. A.; Taylor, R. J. K. Tetrahedron Lett. 2002, 43, 6185-6187 and references therein.
19. (a) Barluenga, J.; Tomas, M. In Advances in Heterocyclic Chemistry; Katritzky, A. R., Ed.; Academic Press: London, 1993; Vol. 57, Chapter 1, pp 1-81.
20. (b) Boger, D. L.; Weinreb, S. N. Hetero Diels-Alder Methodology in Organic Synthesis; Academic Press: London, 1987; Chapter 9, pp 239-299.
21. 1H NMR and can be used as a reference in 2D NMR to identify other signals (see Supporting Information). Final proof of the structure of tetracycles 4 was found when an X-ray crystal structure of 4j was obtained.
22. The CCDC 244632 contains the supplementary crystallographic data for compound 4j. These can be obtained free of charge via www.ccdc.cam.ac.uk/ data_request/cif, or by e-mailing data_request@ccdc.cam.ac.uk.
23. So far we have explored the use of amides derived from triazine 1c and chiral amines. The best de obtained to date was 10%, using the amide synthesized from 1c and (1R,2R)-2-benzyloxycyclopentylamine.